


Company Girl

by kittenofdoomage



Category: Supernatural
Genre: Angst, F/M, Fluff, Oral Sex, Sex, Smut, it's a terrible life au, work rivalry
Language: English
Status: Completed
Published: 2019-07-18
Updated: 2019-07-18
Packaged: 2020-07-08 03:57:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,568
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19863118
Author URL: https://archiveofourown.org/users/kittenofdoomage/pseuds/kittenofdoomage
Summary: You love your job but there’s one problem you’re struggling to deal with. Dean Smith. The office hotshot who drives you crazy. When your boss assigns you to the same project, you think it’s going to go one of two ways… what happens when something completely unexpected throws you?





	Company Girl

Your scream bounced off the thin walls of the apartment as you slammed the door, sinking down with your hands over your face. Across the room, your roommate eyed you with a smirk, knowing exactly what had you returning in such a state.

“Dean Smith?” she ventured and you groaned.

“Dean,” you grunted, “ _ fucking _ Smith.”

Caitlin chuckled, closing her Kindle and dropping it onto the cushion next to her on the loveseat. “What did he do this time?”

“Breathed,” you snapped back, storming into the adjoining kitchen for a can of soda. When you returned, Caitlin was sitting expectantly, waiting for the oncoming rant. “He just can’t let anything go, Cait. This morning at the presentation, he brought up that mess with the Sinclair account from three years ago!”

Her confused look had you calming. “You mean when you found out one of the partners was passing information to a rival firm, right?”

“Yeah,” you sighed, flopping down onto the hideous patterned beanbag that your aunt had decided was a perfect apartment warming gift for two young women. “But he didn’t put it like that.”

“How did he put it?”

“Well, he…” Flinging one arm over your face, you groaned. “It the way he said it! You had to be there. And then he’s with the whole ‘ _ sweetheart _ ’, and paying me compliments with that cocky smirk on his face!”

“You really don’t like him, huh?” Caitlin sounded amused and you frowned, lifting up slightly. “Come on, Y/N. I’ve said it before, you just gotta bang him.” With a roll of your eyes, you were getting to your feet, shaking your head at your best friend. “Hate sex. Take out all those frustrations -”

“I’ve heard enough,” you grunted, walking toward your bedroom. “I’ve told you before that sex doesn’t solve everything.”

Caitlin started to giggle, picking up her Kindle again. “Seems like the perfect solution to me. Although, you could always just be civil and  _ talk _ to him.”

Scoffing at the suggestion, you paused in the doorway. “If Dean Smith was in any way a sociable kind of being, then sure. But he’s not. He’s a stuck up tight ass that eats too much kale and quinoa and wouldn’t know fun if it bit him in the ass.”

She was staring at you, one eyebrow arched high. “Oh yeah. There’s no tension there at all.”

“Gah!” You threw your hands in the air and stomped off, your best friend’s laughter ringing in your ears. With any luck, the next project you take will be solo and you could avoid seeing Dean and his smug stupid face for a few weeks.

*****

“Good morning!” Claire the intern was bright and bubbly as usual, dropping your coffee onto the table with a smiley face drawn on the side. “How was your weekend?”

“Quiet,” you shrugged, thumbing through your mail. “Did everything get sent off on Friday?”

“Absolutely,” the younger woman replied, taking your outgoing mail when you offered it. “You need me to do anything else?” You shook your head, opening your mouth to say thank you, cut off when the elevator doors opened and Dean Smith strode in, briefcase in hand and dazzling smile on his face. 

“Good morning, ladies,” he crooned, eyes twinkling as he walked by them and into his office. You were too busy scowling to reply, making a noise of disgust when the door closed behind him.

“Y/N?” Claire asked, catching your attention. “Is everything okay?”

“The nerve of him,” you growled, shaking your head.

“What did he do?”

_ Nothing _ , your mind provided but you stiffened, forcing a polite smile onto your face. “I don’t think I need anything else today. You can work on the back projects if you’d like.” Realizing the question wasn’t gonna be answered, Claire smiled back, tilting her head. 

“Sure!” The prospect of having her work included in a final project sent her scurrying off. You liked Claire. She’d been a nightmare to start with but once she was in a creative mood, the ideas she had were fantastic. 

A few hours into the morning, you were buried in paperwork and contracts when a call came through. It was Dean, not Claire, who knocked on the door, smiling his irritating smile at you. “Hey, er, Zach’s asked to see us.”

“Why?” you demanded, immediately on the defensive. Dean blinked, shrugging uselessly, and you scowled, getting to your feet. “Fat lot of good you are.” Pushing past him, you marched across the office floor, stopping at Zachariah’s open door, spotting him stood by his desk. “You wanted to see me?”

“Yeah,” Zachariah waved you in, frowning when you went to shut the door. “Where’s Dean?”

Dean appeared at that moment, giving you an annoyed look as he shouldered his way into the room. “He called both of us,” he pointed out.

“Sorry,” you mumbled, “must have misheard you.”

He looked entirely unconvinced by that statement, shaking his head and walking toward one of the two chairs opposite Zachariah’s desk. You finished closing the door, remaining silent as you took the other seat, both of you looking up at your boss expectantly.

“We got a new contract. Big name. Big money. And I need my best on it. Which happens to be you two.” The old man folded his arms over his chest, looking at each of you in turn. “Is you two working together going to be a problem?”

Swallowing, you shook your head, seeing Dean do the same out of the corner of your eye. Zachariah narrowed his gaze, chewing the inside of his mouth.

“Are we sure? Now’s the time to voice your objections, kiddos. This is a big account and I need to know it’s in safe hands. You gotta work as a team on this one.”

Dean shifted in his seat, clearing his throat. “I have no objections. We can work together.”

“We can,” you said suddenly, surprised at your own outburst. “Absolutely.”  _ Whatever game Dean’s playing, I’ll beat him at it _ .

A smile broke out over Zachariah’s face and he clapped his hands together. “Wonderful. Twenty-eight days, I want a full presentation, 10am on the 16th.” You stood up, nodding in acknowledgement. Your boss shooed you out and you hurried out of the office with Dean behind you, stopping in the corridor when the door was closed.

Dean’s green eyes sparkled with amusement when he looked at you. “So, big project. Big money.” He slouched, stuffing his hands in his pockets. “We should get started sooner rather than later.”

“What, now?” 

He grinned. “No time like the present.”

“I can’t,” you whimpered.

“Can’t or won’t?” he teased and you glowered at him, balling your fists at your sides. “I mean, I can always start coming up with a few ideas -”

“No,” you breathed. “I really can’t this afternoon, I have a meeting I can’t miss.” Chewing your lip, you tried to think of something on the spot before he could, wanting to keep control of the situation. “Er, do you know the pizza parlour on 7th and Columbia?”

“Sure,” he nodded, frowning, “why?”

“Seven pm tonight,” you instructed, turning away from him. “And bring your laptop!” 

*****

You’d never been so panicked about meeting someone in public. Dean had been nothing but a thorn in your side since you’d joined the firm, both of you juniors in your field. That was so long ago now, it was hard to imagine yourself as that nervous kid again.

Clashing with him wasn’t an entirely bad thing. The confidence you gained from your little spats, the underhanded compliments and flirting, made it easier to deal with worse specimens. And you’d met far worse than Dean Smith; you just didn’t normally have to deal with them on a daily basis.

You still hadn’t figured out what it was about him that got you so riled up. Caitlin was absolutely wrong about you liking him in  _ that _ fashion. You refused to even consider it.

She wasn’t home when you got back from work and you were glad to dodge that bullet. If she knew where you were going, you’d never hear the end of it. Even if it was absolutely  _ not _ a date.

That didn’t explain why you were so nervous and why you couldn’t decide what to wear. Romeo’s Pizzeria was only a five minute walk but you wanted to be comfortable, as well as look good. It didn’t matter that it was Dean, and he wasn’t the reason you wanted to like nice.

“It’s just in case,” you muttered to yourself, staring at the full-length mirror propped against your closet door. “Might bump into Chris Evans or something. And Mom always told me to wear matching underwear in case of an accident. Paramedic might be cute.”

“Are you talking to yourself?”

Caitlin’s voice from the open bedroom door made you jump and shriek in surprise. The other woman’s eyes narrowed as she took in the form-fitting deep crimson shirt, stretched tight across your breasts, paired with a black cotton skirt that had a slit to mid-thigh. 

You grinned sheepishly, “I wasn’t expecting you to be here.”

“Work was quiet, Jen sent me home,” she shrugged, moving into the bedroom with her arms folded across her chest. “You have a date?”

“No,” you blurted out, quickly enough to make her even more suspicious. “Work thing.”

“Oh? What work thing?”

You blanked, scrambling for something that would make sense. “Employee of the month.” Her face spoke volumes and you groaned, grabbing your jeans again. “I’m meeting Dean.”

“What?!” The expected outburst almost made you laugh but you held your composure, heading for the bathroom. “Y/N, wait -”

“No, you’re right, this looks too much like something I’d wear for a date. Jeans and t-shirt is better, right?”

She stared at you, shaking her head. “Where?” You blinked at the question. “Where are you going?” Caitlin elaborated. “Please don’t tell me it’s Romeo’s -”

“I like it there!” you defended. “And it’s comfortable, and Stanley knows what I like. Plus, it’s the best pizza in the district.” Caitlin rolled her eyes. “Are you saying I should stick with the skirt?”

“No. But you shouldn’t go with the jeans.” Darting across the room, she delved into the dresser, obviously searching for something. When she held up her prize victoriously, you gaped in horror. “This. With that sexy red plaid you have. Something tells me Dean is a red kinda guy.”

Shaking your head, you turned away. “No. Na-uh. No way am I wearing booty shorts.”

“They’re not booty shorts!” she giggled. “They’re the Daisy Dukes I got you that you refused to wear outside.”

“And guess what?” you snapped. “I’m still refusing to wear them outside.”

“Look, borrow my brown cowgirl boots. He’s from Kansas, right?” You nodded dumbly and Caitlin grinned. “Then something tells me, he’s gonna be too distracted by your tits in that shirt than by whatever project you’re working on.”

“Are you telling me to flirt to get the upper hand?” you demanded, staring at her like she’d gone mad. Her smile grew as she nodded, tossing you the shorts. You caught them, giving her a dubious look. “You know I can’t flirt for shit, right?”

Caitlin winked at you as she made to leave the bedroom. “Just be yourself. He won’t be able to resist.”

*****

He was early. 

You stood across the street, your stomach a bundle of nerves as you watched him chatting with one of the servers through the big windows. It was a comfortable little restaurant with eight or nine booths and bar stools along the serving counter, and of all the places Dean could have sat, he’d managed to pick your favorite booth.

It was opposite the train station, where you could see couples reuniting, families saying goodbye… your version of departure lounge people watching. 

Taking a deep breath, you crossed the street, cringing at the loud bell as you entered Romeo’s Pizzeria. Stanley was at the welcome booth, his toothy grin a reassuring sight in an uncertain situation. “Miss. Y/N!” 

“Hey, Stan,” you greeted, giving him a little wave. “I’m, er, meeting someone -”

“Ah, yes. The young man. Very pleasant lad.” His eyes twinkled and you felt your cheeks heat with embarrassment. “He’s already in your favorite booth.” Gesturing toward the booth Dean sat in, with his back to you, Stanley narrowed his eyes. “Would you like me to send Jimmy over to take your order?”

“Sure,” you nodded, “thanks, Stan.”

Turning away, you took a few quick steps toward Dean before nerves slowed your pace. He wasn’t dressed in a suit, which surprised you - you weren’t sure he owned anything else. Dress-down Friday wasn’t a thing for him.

He turned as you approached, smiling when he saw you. “Hey,” he got to his feet, “you’re here.”

For an awkward second, you stood facing each other, unsure what to do. Dean swallowed, gesturing to his laptop.

“You wanna get started?”

Down to business. That, you could work with. That was a comfort zone.

“Sure.” 

_ First step, bigger dialog than _ ‘ _ sure _ ’, you scolded yourself internally, forcing the smile to stay on your face. Dean settled back into his seat as you slid into the other side of the booth. “I ordered a couple of the chocolate shakes. Stanley said they’re your favorite and also that they’re the best in the city.”

You chuckled, nodding. “They really are. Have you eaten?”

“No,” Dean confessed, one hand on his stomach. “Didn’t have time after I left the office. Pretty much gym and shower.”

“Gym?” you asked, raising an eyebrow, unable to stop your gaze dropping to the definition of his chest through the black Henley that suited him far too well. “Worried a slice of pizza will make you a slob?”

He laughed, shaking his head. “No, I just usually go to the gym on Monday. It’s quiet, it’s not crowded.” Shrugged, he picked at the menu in front of him. “Not a fan of crowds.”

It was getting too personal and the initial discomfort you’d felt returned. Dean cleared his throat, picking up the menu.

“Why don’t we order,” he suggested, “and then we can get down to business. I had a few ideas but I wanna know what you think of them first.”

“Oh,” you blinked, smiling nervously. “Sure.”  _ You’re doing fantastic _ , your inner monologue provided sarcastically, sounding a little too much like Caitlin. “I usually have the thin crust meat feast.” Dean grinned, looking up at Jimmy when he approached the table.

“Hey, Y/N. Can I take your order?” Jimmy beamed - he was fresh out of high school, Stanley’s nephew or grandson, or something, you’d lost track. The kid was sweet, lanky in a way that made you think he’d be huge when he was fully-grown. 

“We’ll get a large meat feast to share,” Dean interjected, leaning in a little. “If we get two, I’ll end up eating the whole thing,” he commented and you smiled.

“I normally only get a small,” you whispered. “The calories in the shake more than make up for it.”

Jimmy dotted down the order, humming under his breath. “I’ll be right back with your shakes.” He turned, scurrying back off to the kitchen to give the order to Joshua, another of Stanley’s relatives. You weren’t sure, but you thought every person who worked there was related to the seemingly ageless man.

“It’s nice here,” Dean murmured, tapping at the keyboard on his laptop. “Good place to work.”

“It’s quiet,” you replied, shrugging as you met his eyes with a smile. “Not a fan of crowds.” He smirked when you parroted his words back to him but he didn’t say anything, moving the laptop so you could see the screen. “Show me these ideas.”

Dean nodded, tapping another few keys. “Did you have a chance to think over the proposal specs?”

“I did,” you sighed. “The meeting I was in was exceptionally boring. Annual statistics and improvements. I have to go as part of my contract.”

He pulled a face. “I’d fall asleep.”

You giggled, sitting back when Jimmy promptly returned with the shakes, setting one in front of you and one in front of Dean. Your colleague’s eyes went wide at the size of it, making you laugh harder. “Told you. Calories.”

“I’m gonna need about three thousand crunches to work this off,” he groaned.

“Yeah, but it tastes better than kale,” you teased; he laughed, gripping the straw between his long fingers, leaning forward to wrap his lips around the tip. His cheeks hollowed as he sucked the milkshake up through the straw and you knew you should have stopped staring at least three seconds before but you couldn’t tear your eyes away.

“Oh,” he whispered, “God, that is good.” The sound he made as he took another long drag of chocolatey goodness was positively pornographic and you finally looked away, sipping at your own shake. “Stanley was not lying.”

You needed to get this back on track. The Dean sitting with you was an entirely different entity to the Dean Smith you knew from the office. He was casual, relaxed, cheerful and fuck, you didn’t want to admit it, but he was incredibly attractive.

_ He’s an ass _ , your brain reminded you,  _ nothing but a pain you have to deal with. Remember how angry he got you at that last board meeting? _

“We should get to work,” you rushed out, pushing your shake to the side. “Time’s a wasting.”

“Right, right,” Dean muttered, reluctantly doing the same with his beverage. “Work. Let’s get it done.”

*****

It was pure hell.

You’d spent three hours pouring over project ideas, sharing the pizza and enjoying your shakes and it was hands down the best time you’d had in a long time. So good, that you didn’t even notice the time until Stanley was out with his broom sweeping up.

“Jesus,” you mumbled, “look at the time.”

Dean’s head came up from the computer. “Huh. I didn’t realize.”

“You kids about done?” Stanley asked cheerfully. “I gotta lock up.”

“Yeah, sorry, Stan,” you got to your feet, “we got so caught up -”

“Looked like you were havin’ fun to me,” Stanley winked, moving off with his broom. Dean was already putting his laptop away, grabbing his jacket to fish out his wallet. He threw a few bills on top of the total amount, smirking up at you.

“Definitely the best pizza this side of the river,” he said, giving Stanley a thumbs up over your shoulder. “C’mon, I’ll give you a ride home.”

You didn’t argue with that, seeing the hour. The walk home wasn’t far but it was dark and the neighborhood wasn’t a great as it used to be. Bidding Stanley goodbye, you let Dean hold the door for you, ducking your head a little bashfully as you walked by.

“My car’s just around the corner,” Dean informed you and you nodded, folding your hands in front of you as you walked a pace or two behind him. Turning around the corner of the block, you were surprised to see a sleek black classic car, the only one parked there.

“I thought you drove a Prius?”

Dean chuckled. “No, that belongs to the guy I carpool with. Sam in Tech Support?” You shrugged, not knowing who he was talking about. “Um, he’s about six foot zillion with floppy hair and a bright yellow shirt.”

“Oh!” You grinned, nodding as you remembered seeing him about. “He fits in a Prius?”

Another chuckle left Dean’s lips as he opened the passenger door of the classic car, gesturing for you to get in. Closing the door like a proper gentleman, he trotted around the front of the car, sliding into the driver’s seat before sliding his laptop bag underneath.

“My Baby isn’t built for commuting. Plus, Sam is guaranteed a parking space, and my girl is safe in my garage all day where she doesn’t get scratched or damaged.”

“You really love this car, huh?” 

He raised an eyebrow, giving you a cheeky smile. “She’s my Baby.”

You giggled, watching him turn the key in the ignition. The car roared to life, her throaty engine sending vibrations through the entire vehicle. Dean grinned, focusing on the road ahead.

It was only a few minutes before you were directing him to your apartment building, time stretching into discomfort as he slowly pulled the car over to the curb. Turning the engine off, Dean turned to look at you.

God, you didn’t realize how bright his eyes were. How the corners of his mouth scrunched up into the most adorable dimples when he smiled. The entire evening, he’d been polite and well-mannered, listening to your every idea and never critiquing it. It was like you’d gone to dinner with a different person.

“You okay?” Dean asked, leaning over a little.

“I… don’t know,” you admitted, biting your bottom lip as you considered your next words. “This feels like a date.”

For a second, he didn’t say anything and your stomach sank. This was it. He’d fooled you and this was -

“It’s not a date if we don’t kiss,” he pointed out.

Your instant reaction was a giggle and Dean smiled, the stretch of his lips slow, his eyes wrinkling at the corners. When your giggles subsided, you shook your head, feeling a little more relaxed. “I just… I don’t understand how you’re like this but… you’re like that at work.”

“Like what?” he asked, seemingly puzzled.

“Like a prized asshole,” you muttered. His cheeks darkened, his gaze darting away in a guilty fashion and you pulled back. “You… were you faking it?”

A nervous little laugh left him and he looked down, reaching over to take your hand. “We started a few weeks apart, right?” You nodded, confirming his statement. His thumb stroked over the back of your fingers; a shudder ran down your spine. “The second you walked into my office to introduce yourself, I didn’t know what to do. I mean, I know what I wanted to do -”

His lewd tone made you smile when it should have made you feel nothing but disgust.

“But that hasn’t worked out so well in the past,” he mumbled, an unknown pain flashing over his face. “So I thought it was probably a good idea that you hated me. And you didn’t make it easy - do you have any idea how good you are at your job?”

“You were mean to me because you like me?” you asked, avoiding the praise; Dean nodded, not meeting your eyes. “Did you ever leave elementary school?” The way you said it made him laugh again and you grinned. “You’re an idiot. Like, a whole idiot. One hundred percent.”

“Yeah,” he agreed. “I am.”

The kiss was unexpected and for a second, you went stiff as a board, eyes wide open. Dean’s lips were warm and soft, the faint taste of chocolate on them - you yielded, relaxing into him as his hand cupped your cheek.

When he broke the kiss, you were breathless and hornier than you might have ever been in your life.

“Now,” he whispered, his lips still lingering against yours, “it’s a date.”

You managed a squeak in response, leaving him to withdraw laughing under his breath. Your heart hammered in your chest, your fingers were tingling and you were so tense, you could feel the beginnings of cramp in your calves.

“It’s really late,” Dean pointed out, “and we do have work tomorrow.”

“We do,” you sighed. “Ugh.”

“Hey,” he started, looking a little nervous as he glanced over at you. “Maybe, tomorrow night? Maybe I can take you to my favorite spot maybe?”

“How many times are you gonna say maybe?” you teased, smiling when his cheeks turned a slightly darker shade. “I’d love to.”

Dean didn’t pull away as soon as you got out of the car. He waited, the engine still off while you walked to the door. You unlocked it, slipping inside and waiting for the security lock to click back into place. Only then did he start the car and slowly pull away.

There was a small chance you floated up the stairs to your shared apartment and you were lucky that Caitlin wasn’t anywhere to be found. You didn’t think you wanted to recount the evening right then; you were still processing the sudden turn of events.

Tomorrow was definitely going to be interesting.

*****

“Really?”

Caitlin was waiting for you in the kitchen the next morning, two fresh cups of coffee on the breakfast bar and the smell of warm blueberry muffins permeating the entire apartment. 

“Really what?” you asked innocently, slipping into the stool opposite her. She glared, folding her arms across her chest. “Oh, you wanna know about last night.”

“Duh.”

Shrugging, you picked up the coffee she’d made, avoiding eye contact over the rim of the cup. “Nothing to tell.”

“Bullshit,” she scoffed.

“Nothing happened, Caitlin. We got a lot of work done and it was… pleasant.” The smile that twitched on your lips gave you away and she stared with wide eyes. “What?”

“You had a good time. With Dean. The same Dean you’ve been doing nothing but complaining about since you met him.”

You shrugged again, pouting indifferently. “I guess it was just different in an out-of-work situation. He’s…”

“Oh, my god,” Caitlin interrupted. “You really like him.”

“Shut up.”

She laughed at your abrupt response, mumbled into your drink. You scowled when she didn’t stop, chuckling away as she passed the basket of muffins she’d been obscuring from sight. “So, come on. I love being right.”

“We talked,” you admitted, lowering your cup. “And… there may have been a kiss.”

“Damn, girl,” Caitlin giggled. “Don’t spare me the details.”

“That was pretty much it. He drove me home, we kissed, and he’s taking me out for dinner tonight.”

“Second date, huh?”

You swallowed, turning your cup in your hands. “I guess.”

The other woman narrowed her eyes. “You’re nervous?”

“About work,” you sighed, sipping at your drink again, swallowing the mouthful before continuing. “What if this is all a prank? I mean, last night I was on cloud nine but… me and Dean have never done anything but butt heads and now -”

“Feeling a bit  _ She’s All That _ ?”

You smiled at the reference, shaking your head. “No. I mean, we’re adults. Adults don’t do that sort of thing, right?” Caitlin shrugged which was slightly less than helpful and you sighed again, finishing your coffee and grabbing a muffin. “I guess I’ll find out in about thirty minutes.”

“I’m sure he’s not playing games, Y/N,” Caitlin said, offering a soft smile. “You’re pretty awesome, any guy could see that.”

“You’re the best cheering squad a girl could ask for,” you replied, kissing her on the cheek before turning away.

The commute to work was quick and you pulled your car into the garage, heading up to the top level. Pulling into your usual space, you frowned as you noticed the empty spot where the Prius would normally be.

Dean wasn’t in his office when you knocked and none of the other staff had seen him. Finding Zachariah in his office, you were dismayed to find he had no idea of his whereabouts. 

It wasn’t until noon that Dean walked into the office, dressed in his usual suit but missing his usual composure. His hair was a scruffy mess and one leg of his pants was smeared with something black. He gave you a smile as he walked by, directing himself straight to the boss. 

Concerned and confused, you retreated to your office, busying yourself with paperwork and the ideas Dean had emailed to you the night before after your brainstorming session. Minutes ticked by and your concern grew, only to be completed obliterated when Dean appeared in the doorway of your office.

He smiled brightly, entering and shutting the door behind him. “Everything okay?” you asked, worry creasing the line between your eyebrows.

“Yeah, I’m good. We, er, had an accident on the way in,” he explained, dropping his briefcase on the small sofa by the door. “Someone ran us off the road and Sam was -”

You gasped. “Oh, god, is he alright?”

Dean chuckled, shedding his jacket. “He’s fine. The Prius…” He hissed through his teeth. “Not so much. Sammy’s lucky he has good insurance.” Moving past the desk, Dean stepped into your personal space, leaning down. You didn’t have a second to panic, the kiss taking you by surprise, his moan stunning you further. “Sorry,” he whispered, pulling back with a smile. “Just… I was thinking about doing that all night.”

Clearing your throat, you managed a meek smile. “We’ve got work to do, Dean.”

“‘Course,” he murmured, retreating to the seat on the opposite side of the desk. “Did you get my email?”

“Yeah,” you answered, tapping through. “I’m really liking this suspension idea, the one you came up with yesterday.”

The atmosphere turned professional and by the time Zachariah was knocking on the door at four pm, you and Dean were almost at a working proposal for the contract already. The older man was pleasantly surprised at the turn of events, happy you were working together so well.

“Keep up the good work,” he encouraged, “knew you’d make a hell of a team.”

“He’s not wrong,” Dean remarked when Zachariah had left - you looked at him curiously. “I mean, if I’d not been an ass -”

“In all fairness,” you pointed out, “I was not the easiest person to work with.”

Dean chuckled, shaking his head. “We’re equally stubborn.” His phone started to ring in his pocket; he pulled it out and frowned at the screen. “I’m gonna have to take this.”

“No worries,” you shrugged. “I’m gonna head home.”

“I’ll pick you up at six?” he asked quickly, accepting the call as he headed for the door.

“Sure.”

The door closed behind him and you sighed, leaning back in your chair. Dean wasn’t wrong about the work you were doing being amazing. He was just as good at the job as you were and putting your heads together was working wonders. 

Packing up your things, you headed out of the office, not seeing Dean anywhere on your way out. By the time you’d reached your car, you were wondering who had called him that meant he had to pick up so urgently, and by the time you’d gotten home, the doubts and fears were resurfacing. Other than the surprise kiss this morning, there hadn’t been any other touches or glances or…

You’d been busy working. You probably wouldn’t have noticed if there was and that was only the spark for a new line of anxiety. If Dean was serious about this, and you didn’t show him any enthusiasm -

God, you were sabotaging yourself before you’d even started anything.

Caitlin was home when you got in but she didn’t dog you for any details. When you asked her for help picking an outfit, you didn’t mention any of your worries - she’d only tell you that you were being an idiot. And probably repeat her earlier ‘ _ I told you so _ ’ with regards to Dean.

Without knowing where he was taking you, you were completely clueless as to how to dress. Caitlin suggested jeans and a form-fitting shirt that you could button up to be a little more respectable, just in case. 

Dean arrived ten minutes before six, the Impala rumbling on the curb outside. You were panicking even more and when the buzzer rang, you were nearing hyperventilation. Caitlin answered it, inviting him up before you could stop her.

“I wanna know what all the fuss about,” she defended, patting your shoulder. “You need to calm down.”

“I haven’t been on a date in years, Cait!”

“You went on one last night. With this guy.”

“That doesn’t mean -”

The knock at the door made you jump and Caitlin darted away to answer it, smiling as she greeted Dean. “I’m Caitlin, Y/N’s roommate. I’m sure she’s told you all about me.”

Dean laughed nervously, shaking her hand when she offered it. “Pretty sure you’ve heard the worst about me.”

“Oh, you betcha.”

You glared at your roommate, who smiled sweetly. “You’re early,” you squeaked and Dean smirked, rubbing one hand over the back of his head.

“I drove around the block three times,” he confessed. “I was nervous.”

Caitlin was stood behind him as he explained himself, making faces and gesturing obscenely. You forced a laugh, shaking your head and taking Dean’s arm. “We should get going. Do we have reservations?”

“Yeah,” he replied, “sort of. You’ll understand when we get there.”

*****

It wasn’t long into the drive that the streetlights started to become fewer and fewer, until you were right in the suburbs. The houses were further apart and after about forty-five minutes, the houses became farms.

“If I didn’t know better,” you murmured, looking around the dark landscape, “I’d think you were taking me out into the middle of nowhere to murder me and steal all my ideas.” He laughed, shaking his head. “But everyone knows I’m with you so it would be a really stupid plan.”

“I promise,” he assured you, “this place is amazing. It’s not far now.”

You shrugged happily, watching the horizon for any sign of where he was taking you. When a few pink lights lit up the road ahead, a sign directing you to  _ The Roadhouse _ , you were a little surprised. “A truck stop?”

“Jeez, don’t call it that when we’re in there,” he scolded, looking a little horrified. “My mom’ll kill you.”

“Your mom?” You blinked in surprise, unsure if you liked the idea of meeting his mother so soon.

“She thinks I’m just coming out for dinner with a colleague. She won’t bug us,” he dismissed. “But the food here is better than anything you’ll eat, ever.” He looked so sincere as he glanced at you, guiding the Impala into the parking lot beside twenty-odd other trucks and pickups. 

“I’m dubious,” you muttered. “I’ve seen your lunches.”

“And don’t mention that,” Dean rushed out. “Mom thinks any food is good food. She’s the live-life-to-the-fullest type.” You stared at him as he smiled bashfully. “Look, you showed me your favorite place to eat. And this is mine. My mom is awesome, I promise.”

Nodding, you smiled at him. “Well, come on then, I haven’t eaten since that tuna sandwich at lunch.”

“Remind me to repay you for that,” he grunted.

The Roadhouse, from the outside, looked like an old building that had seen better days. When you stepped inside, it was something like you’d imagine an Old West saloon. There were a few customers in, mostly men, a few older couples, and a blonde woman tended the bar, chatting amiably with a middle-aged gentleman in a ridiculous cowboy hat.

“Dean!”

The blonde woman noticed him, smiling as she waved him over. Despite Dean apparently telling her that you were a friend from work, the judgemental once-over she gave you confirmed that she was probably aware of her son’s deception.

“Mom,” Dean greeted, slipping onto a bar stool. “This is Y/N, from work.”

“Hi, Y/N,” Ellen grinned. “I’m Ellen. I’m gonna go right ahead and apologize if my son has ever been an ass to you - that ain’t the way his momma raised him.” You giggled, shaking your head.

“He gives as good as he gets,” you replied and the older woman beamed.

“Right then,” she slapped a hand on the bar, “what’ll it be, kids?”

*****

When you’d first walked into the diner and sat down with Dean, you’d panicked that there would be nothing for you to talk about beyond work. As it turned out, Dean wasn’t just a cardboard suit with a pretty face.

His family were pretty welcoming too. His younger sister Jo had returned home shortly after you’d arrived and you couldn’t believe how tiny she was compared to her brother. But it appeared they had the same dry sense of humor and she was just as friendly as his mom.

By the end of the night, you’d discovered that he had a serious obsession with his car, he loved pie more than pretty much any food except the triple bacon and cheese deluxe that his mom made. His music taste ran from somewhere in the late sixties to 1979 and not far beyond that, which was slightly adorable.

It was after eleven by the time Dean suggested you leave, making a quip about it being a school night. His mom waived the tab, despite his objections, ignoring him entirely as she said goodbye to you. “You’re welcome any time. Dean never brings any friends home these days.”

Dean’s cheeks were fiery red as you laughed your way to the car, buckling yourself in with a smile still on your face. “Laugh it up,” he mumbled, although his lips curled up into a grin. “I’m glad she likes you.”

“I like her too,” you replied, giving him a slightly doe-eyed look. “The food was fantastic.”

Raising one eyebrow, Dean turned the keys in the ignition, pulling the car away from the diner. “Now you see why I try and behave at work. I come home a lot, and Mom…. Mom’s a feeder.” You laughed again, folding your hands in your lap.

“It’s nice you come home often,” you said, glancing out the window to watch the dark scenery. In the distance, the city glowed like a beacon; you’d always dreamed of living in the quiet countryside one day.

“I don’t have many friends in the city,” Dean admitted quietly. “I mean, there’s Benny but he works nights. And Sam is all wrapped up in his girlfriend.” He smiled over at you. “I sound like a loser.”

“Hey, I don’t have a raging social life,” you pointed out. “I mean, this was my first proper date in… forever? Kinda don’t want it to end.”

Dean grinned at that, reaching over to take your hand, lacing his fingers through yours. “Me either.”

Taking the plunge, you tried to steady your breathing, feeling your heart racing out of control. “Does it have to? Even if it’s a school night?”

He chuckled, shaking his head. “Not if you don’t want it. I’m fairly convinced Zachariah will let us work out of office tomorrow.”

“The thing is,” you whispered, slightly embarrassed, “my roommate -”

“Yeah,” he drawled in agreement with your non-verbal statement. “Rental prices suck these days. Lucky for us, I got a loft apartment all to myself.” A rush of heat between your thighs made you clench them together and you nodded, a shaky smile on your lips.

“I better text her,” you mumbled, dragging your phone out of your pocket and firing off a quick message to explain you wouldn’t be home. Caitlin replied in seconds, her message containing only eggplant and squirt emojis, which made you roll your eyes.

“What did she say?” Dean asked, making your cheeks heat in shame as you showed him the screen. He simply laughed under his breath, not making any comment at all.

The neighborhood Dean’s loft was in wasn’t the  _ worst _ neighborhood in the city but it certainly wasn’t one you’d walk alone through. He pulled up by a dilapidated building and you peered out, concerned about where he was taking you now.

“You sure you’re not a serial killer?” you mumbled, making him chuckle as he turned off the engine. 

“It doesn’t look so bad inside,” he promised, opening the door. You waited, letting him do his gentleman thing, opening your door for you. With a flourish, Dean bowed down, circling his hand in the air in some sort of lordly manner that made you giggle. “My lady.”

Tipping your head ever so slightly, you took the offered hand, climbing out of the car. Dean locked it, hooking his arm through yours.

He wasn’t lying about the inside of the building. Once you’d made it through the heavy steel doors, there was a set of stairs. There were three floors, each containing apartments. “How many people live here?”

“A few,” Dean replied, leading you toward the staircase. “No elevator I’m afraid.”

“This looks really modern,” you commented, eyeing the sterile steel surroundings. You were fairly certain the plants dotted around the place were fake but you didn’t say anything.

“The guy who bought these warehouses is renovating them all from the inside out. Rents to professionals, young couples who don’t want a house. Lot of the people in this unit work in the city and don’t wanna commute.”

“You commute,” you pointed out and Dean chuckled.

“Yeah, but if I commuted from my mom’s place every day?” He hissed, shaking his head as you reached the third floor. This corridor only contained two doors, apartment numbers 8 and 9. “It’d be a nightmare. Sam only lives two blocks over so it’s…” 

“Economical?” you provided; Dean smirked, nodding as he pulled you toward door number 9. “Let’s see your palace.”

It wasn’t what you were expecting. Dean seemed to live a spartan lifestyle - grand windows gave a startling view of the city, lights filling the skyline. His kitchen and living area were combined, both spacious, both sparsely decorated. One photo of his mom and sister sat on the coffee table, along with a copy of a classic cars magazine.

“It’s very clean,” you muttered, a little surprised.

Dean grinned. “I like things neat and tidy. Besides, you haven’t seen my bedroom.”

“Is that an invite, Mr. Smith?” you teased, giggling when he pulled you into his arms, kissing you softly. “Because I’m very inclined to accept.”

“We’re not gonna get any work done tomorrow, are we?” he murmured, lips so close to yours you could feel his warm breath. “Not that I’m going to complain -”

Pressing a finger to his lips, you pulled back, remaining his hold and smiling up at him. “You wanna keep talking or take me to bed?” His answering smile was only a split second before he was scooping you up, kissing away your protest as he carried you to the bedroom.

Clothes came off and joined the ones already scattered across the floor. It was a stark contrast compared to the rest of the apartment but you didn’t particularly care when Dean was unhooking your bra, catching one stiff nipple as it was revealed to him. You squeaked, grabbing his head with both hands as he busied himself teasing your breasts, tossing your bra away into the mess of clothing.

His hands cupped your ass, lifting you again, his face buried between your tits. You whimpered, holding on for dear life as he crashed the both of you into his ridiculously comfortable mattress. Sinking into it, you hummed as Dean kept biting, licking, sucking at your sensitive skin.

“Get these off,” he growled, plucking at the waistband of your pants. “Want you naked.”

You scrambled to obey, which was easier said than done when Dean couldn’t keep his hands or mouth off of you for five seconds to let you move. Eventually, you kicked them off the end of the bed, pulling him up to kiss him forcefully.

“Let me taste your pussy, baby,” Dean murmured low in his throat, barely parting from your lips to speak. Your only answer was breathy moan and when he pulled away, you pouted, watching him lay back on the bed. “C’mere.”

He flung one arm out and you pushed yourself up, frowning at him. “I thought -”

“I wanna taste you,” he rumbled, patting his chest. “And I wanna watch you cum.”

It felt like every cell in your body had turned to jello. You shivered as you moved, hesitantly straddling his chest. Dean groaned when your thighs slipped over his shoulders, using his hands to drag you closer, making you yelp in surprise when his tongue swiped over your slick folds.

“Fucking gorgeous,” he hummed against your cunt, sending a shudder down your spine. Leaning forward, you braced yourself against the headboard, unable to resist looking down to watch Dean feasting on you. His fingers were digging into your ass, his lips wrapped around your clit, focusing only on that particular bundle of nerves.

A warm tingle started right down in your belly, growing with each touch of his tongue. You closed your eyes, gasping, worrying for a second that you might crush him with your thighs but Dean seemed insistent on getting what he wanted.

By the time you fell over the edge, you were rolling your hips against him, grinding onto his face as you cried out. Dean snarled, pressing harder; your hands slipped from the headboard and you fell backwards, only to be caught in a roll as Dean untangled himself from your slick thighs.

“You taste fucking amazing,” he purred, pulling you flush against his body. You were shaking all over, sweating already, just from a few minutes of his tongue on your sex. “You’re beautiful when you cum.” A shy smile tugged at your lips and Dean ground his hips into you, letting you know how aroused he was - his cock was stretching the capacity of his boxers, twitching every few seconds.

You could taste yourself on his tongue when you kissed him. The eroticism of it made your entire being sing and you lifted one leg, pressing your pussy against his covered erection, making him moan wantonly.

Repeating his earlier actions, you grabbed the waistband of his boxers, smirking at him. “Get these off,” you ordered; Dean laughed, kissing you again as he made quick work of removing the offending undergarment, tossing them carelessly to the floor. He barely had time to lay back before your fingers were wrapped around him, stroking him, testing the weight of him in your palm.

“Fuck,” he groaned through clamped teeth, closing his eyes as he tipped his chin up.

“Do I get to return the favor?” you asked a little shyly. Dean’s eyes popped open, a smile on his lips.

“Not tonight. I just wanna make you cum.”

You shuddered again, feeling the warmth of his body as he pushed you onto your back, settling between your thighs. The tip of his cock brushed your folds and you panicked, slamming a hand into his shoulder. “Condom,” you squeaked.

Dean’s expression changed instantly - he reached for the drawer beside the bed, fumbling around inside. The foil packet he pulled out looked fairly new but he checked the expiry date anyway, grinning when he found it to be perfectly in date.

“Good thing you remembered,” he admitted, “I was getting carried away.”

“We both were,” you whispered, watching as he knelt upright, tearing the condom packet with his teeth and rolling the latex down his thick shaft. It almost looked painfully tight and Dean grimaced, stroking himself a few times to adjust to the feeling.

Leaning over you, Dean captured your lips again, kissing you deeply. You spread your thighs wider, digging your heels into the bed as you wrapped your arms around his shoulders.

“Fuck me, Dean,” you begged softly. Smiling, Dean kept kissing you, distracting you as he lined up.

The first stretch of his cockhead pressing into you made you moan loudly into his mouth and Dean stopped, giving you a moment to acclimate. When your walls squeezed him, he rolled his hips, penetrating you a little deeper. He groaned, muttering something that wasn’t clear, not that you could focus on words right in that moment.

“More,” you pleaded.

Dean rocked into you, giving you a little more. When you repeated the request, he pulled back, easily sinking back in.

Impatience lifted your legs, digging your heels into his ass as you grabbed the back of his head and kissed him. He drove forward under the pressure, growling against your lips when his cock filled you to the brim, the stretch making you arch underneath him.

Both of you stopped, panting as you clung to one another.

“You okay?” Dean asked, concern on his face.

“I’m perfect,” you replied, smiling up at him, still unable to quite believe this was happening. “Don’t stop.”

He grinned, kissing you once more, slowly starting to move. You kept your legs wrapped around his waist, meeting him thrust for thrust. Before long, neither of you were making any noise aside from panting, clutching at each other in a desperate attempt to get closer than humanly possible. You weren’t sure if you came, not properly, but it was pleasurable enough that you really  _ really _ didn’t want it to end.

Dean’s shoulders tensed when your internal muscles squeezed him; he shook his head, gasping against your throat.

“I’m gonna cum,” he grunted, sliding a hand between your sweat-slicked bellies. “Want you to cum with me.”

His thumb found your clit and you bucked, almost headbutting him in surprise at the touch on your sensitive sex. He didn’t lose his pace, going harder if anything and he pushed up with his other arm, drawing your attention for a second to the handsome bulge in his muscles.

“Cum with me,” Dean urged, his thumb working harder at your clit, instantly increasing the pleasure. You flung your arms above your head as you felt your climax building, barely able to keep your eyes open. Dean fucked into you furiously, alternating between watching your face twist in euphoria and watching your pussy take every inch of his dick.

He lost it at the same second you did, feeling the squeeze of your cunt on his shaft. Spilling into the condom, his arm shook with the effort of holding himself up and when he was finally done, he barely managed to keep his weight from crushing you.

You remained oblivious, eyes closed and arms laid out either side of you like some perverted crucifixion, Dean’s cock still throbbing inside you, breasts heaving with the aftereffects of your orgasm. Behind your eyes, you could see stars; it took a few moments to regain your composure enough to open your eyes.

Dean pulled away, withdrawing entirely before kissing you, smiling as he climbed off of the bed. He removed the condom and disposed of it, grabbing a fresh pair of boxers from the dresser. Slipping them on, he rooted through the dresser, emerging with a pair of sweats and a huge shirt.

“You don’t have anything else to sleep in,” he said, offering them to you.

“Well, I normally sleep nude,” you whispered, cheeks heating with the flirtation.

Dean’s grin couldn’t be wider. “That is absolutely fine by me.”

*****

The breakfast things were scattered across the bed, along with some notes and Dean’s laptop. But none of those things had been touched for ages.

You were on your back, legs raised and feet digging into the covers - Dean was between your thighs, eagerly licking and sucking at your sex, pushing you toward your third orgasm before noon. The man had an oral fixation and it wasn’t one that came without benefits.

Licking his lips noisily, Dean looked up, grinning at you as you panted through the last of your climax. 

“You know,” he murmured, lazily dragging his tongue over your clit, earning a little jerk of your hips, “I think this is the start of a wonderful partnership.”


End file.
